Herbicidial composition and method

ABSTRACT

A herbicidal composition comprising a herbicidally effective amount of N-halogenoacylanilino-fatty acid or the ester derivative thereof represented by the general formula: ##STR1## wherein R 1  and R 2  each represents C 1  -C 4  allyl, R 3  represents a hydrogen atom, alkyl having up to 10 carbon atoms, C 3  -C 5  alkenyl, C 3  -C 4  alkynyl or cyclohexyl, R 4  represents lower alkyl substituted by 1-4 halogen atoms and Y represents C 1  -C 3  alkylene, as an effective ingredient, and a herbicidally effective inert carrier.

This is a division of application Ser. No. 235,044, filed Mar. 15, 1972,now U.S. Pat. No. 3,780,090, issued Dec. 18, 1973.

This invention relates to novel N-halogenoacylaniline-fatty acid or theester derivative thereof as an effective ingredient, to a process forproducing the same and to herbicidal composition containing the same.

More particularly, the present invention relates to (1) a novelN-halogenoacylanilino-fatty acid or the ester derivative thereofrepresented by the general formula(I); ##STR2## wherein R₁ and R₂ eachrepresents lower C₁ -C₄ alkyl group, R₃ represents hydrogen atom, alkyl,lower C₃ -C₅ alkenyl group or lower C₃ -C₄ alkynyl group, R₄ representslower alkyl group substituted by 1-4 halogen atom, and Y representslower C₁ -C₃ alkylene group, (2) a process for preparing the compound ofthe formula(I), which comprises reacting anilino-fatty acid or the esterderivative thereof represented by the general formula (II); ##STR3##wherein R₁, R₂, R₃ and Y are the same as defined above, withhalogeno-fatty acid halide represented by the general formula (III);

    R.sub.4 COX                                                (III)

wherein R₄ is the same as defined above and X is a halogen atom, in thepresence of a suitable dehydrohalogenating agent to obtainN-halogenoacylanilino-fatty acid or the ester derivative thereofrepresented by the general formula (I), and (3) a process for preparingthe compound of the formula (I) which comprises reacting alkali metalsalt of halogeno-fatty acid anilide derivative represented by thegeneral formula (IV); ##STR4## wherein R₁, R₂ and R₄ are the same asdefined above, with halogeno-fatty acid ester represented by the generalformula (V);

    Z--Y--COOR.sub.3                                           (V)

wherein Y and R₃ are the same as defined above, and Z represents halogenatom, or with the ester derivative thereof to obtainN-halogenoacylanilino-fatty acid represented by the general formula (I)or the ester derivative thereof and to (4) herbicidal compositioncontaining the compound of the formula (I) as an effective ingredient.

N-halogenoacylanilino-fatty acid and the ester derivative thereofobtained by the present invention are novel, and it has found by presentinventors that they possess strong herbicidal activity which could notbe expected from other analogous publicly known compounds, and extremelyadvantageous selectivity.

That is, the compounds of the present invention have a strongweed-killing effect to a wide scope of weeds and, for example, they havean excellent weed-killing effect to both grassy weeds such asbarnyardgrass (Echinochloa crusgalli), large crabgrass (Digitariasanguinalis), water foxtail (Alopecurus aequalis), annual bluegrass (Poaannua), etc. and broad-leaf weeds such as chick weed (Stellaria media),common purslane (Portulaca oleracea), redroot pigweed (Amaranthusretroflexus), monochoria (Monochoria vaginalis), false pimpernel(Linderna pyxidaria), etc. Furthermore, the compounds of the presentinvention are characterized in that they have selectivity toward variouscrops, and thus, they are capable of controlling weeds without causingany phytotoxicity, for example, to radish, cabbage, pea, sugar beet,burdock, tomato, cotton, wheat, corn, etc.

In addition, the use thereof in a paddy field is extremely effective dueto the greatly strong weed-killing effect thereof, and the compounds arecapable of controlling main weeds growing in a paddy field, such asbarnyardgrass, monochoria, false pimpernel, (Rotala indica), nutsedgesp. (Cvperus difformis), etc. without causing any phytotoxicity totransplanted rice and, furthermore, the compounds have excellent effectof controlling even a perennial plant, slender spikerush which isdifficult to control.

The compounds of the present invention are useful as a herbicide forvarious cereals such as rice, corn, etc., vegetables, fruit trees, alawn, a meadow, forest, non-farming land, etc.

The present invention (1) has been completed on the basis of theabove-mentioned novel knowledge, and relates to a novelN-halogenoacetylanilino-fatty acid or the ester derivative thereofrepresented by the general formula (I) and to their herbicidalcomposition.

The invention (2) and (3) relates to a process for producing the sameand, in the invention (2), N-halogenoacylanilino-fatty acid or the esterderivative thereof can be obtained in general by dissolvinganilino-fatty acid or the ester derivative thereof represented by thegeneral formula (II) and equimolar amount of halogeno-fatty acid haliderepresented by the general formula (III) in an inert solvent such asbenzene, toluene, xylene, ethyl ether, isopropyl ether, ligroin, hexane,acetone, methyl isobutyl ketone, chloroform or carbon tetrachloride,preferably, in benzene, adding dropwise equivalent amount ofdehydrohalogenating agent such as pyridine, triethylamine,N,N-diethylaniline, N-methyl-morpholine, sodium carbonate or potassiumcarbonate, preferably, triethylamine, stirring the mixture for a while,then washing the resulting solution with successive, dilute hydrochloricacid, dilute alkali aqueous solution, and water, and, after drying,removing the solvent to obtain the pure end product in good yield.

In the invention (3), N-halogenoacylanilino-fatty acid or the esterderivative thereof can be obtained by dissolving halogeno-fatty acidanilide derivative in an appropriate solvent such as diethyl ether,isopropyl ether, tetrahydrofuran, dioxane, benzene, toluene or xylene,preferably, in tetrahydrofuran, adding equivalent amount of alkali metalsuch as sodium, potassium, lithium, etc., or alkyl alkali or phenylalkali derivative to form alkali metal salt of halogeno-fatty acidanilide derivative, adding thereto equimolar amount of halogeno-fattyacid represented by the general formular (V) or the ester derivativethereof, stirring the mixture, if necessary, under heating and, afterthe completion of reaction, removing the solvent and inorganic salts toobtain pure end product in good yield.

Examples of each of the starting materials employed in the presentinvention are illustrated below but of course the present invention isnot limited by them.

Anilino fatty acid and the ester derivative thereof:

2,6-dimethylanilino-acetic acid;

methyl 2-6-dimethylanilino-acetate;

ethyl 2,6-dimethylanilino-acetate;

n-propyl 2,6-dimethylanilino-acetate;

iso-propyl 2,6-dimethylanilino-acetate;

n-butyl 2,6-dimethylanilino-acetate;

iso-butyl 2,6-dimethylanilino-acetate;

2-methyl-6-ethylanilino-acetic acid;

methyl 2-methyl-6-ethylanilino-acetate;

ethyl 2-methyl-6-ethylanilino-acetate;

n-propyl 2-methyl-6-ethylanilino-acetate;

2,6-diethylanilino-acetic acid;

methyl 2,6-diethylanilino-acetate;

ethyl 2,6-diethylanilino-acetate;

n-propyl 2,6-diethylanilino-acetate;

2,6-di-n-propylanilino-acetic acid;

methyl 2,6-di-n-propylanilino-acetate;

ethyl 2,6-di-n-propylanilino-acetate;

n-propyl 2,6-di-n-propylanilino-acetate;

n-butyl 2,6-di-n-propylanilino-acetate;

methyl α-(2,6-dietylanilino)propionate;

ethyl α-(2,6-diethylanilino)propionate;

n-propyl α-(2,6-diethylanilino)propionate;

methyl β-(2,6-diethylanilino)propionate;

ethyl β-(2,6-diethylanilino)propionate;

n-propyl β-(2,6-diethylanilino)propionate;

methyl α-(2,6-dimethylanilino)propionate;

ethyl α-(2,6-dimethylanilino)propionate;

n-propyl α-(2,6-dimethylanilino)propionate;

α-(2-methyl-6-ethylanilino)propionic acid;

methyl α-(2-methyl-6-ethylanilino)propionate;

ethyl α-(2-methyl-6-ethylanilino)propionate;

n-propyl-α-(2-methyl-6-ethylanilino)propionate;

n-amyl 2,6-dimethylanilino-acetate;

n-hexyl 2,6-dimethylanilino-acetate;

cyclohexyl 2,6-dimethylanilino-acetate;

n-dexyl 2,6-dimethylanilino-acetate;

iso-amyl 2,6-dimethylanilino-acetate;

allyl 2,6-dimethylanilino-acetate;

crotonyl 2,6-dimethylanilino-acetate;

β-methylallyl 2,6-dimethylanilino-acetate;

n-amyl-2-methyl-6-ethylanilino-acetate;

cyclohexyl 2-methyl-6-ethylanilino-acetate;

allyl 2-methyl-6-ethylanilino-acetate;

crotonyl 2-methyl-6-ethylanilino-acetate;

n-amyl-2,6-diethylanilino-acetate;

sec-amyl 2,6-diethylanilino-acetate;

crotonyl 2,6-diethylanilino-acetate;

β-methallyl 2,6-diethylanilino-acetate;

n-decyl 2,6-diethylanilino-acetate;

cyclohexyl 2,6-diethylanilino-acetate;

n-amyl α-2,6-dimethylanilino-propionate;

cyclohexyl α2,6-dimethylanilino-propionate;

allyl α2,6-dimethylanilino-propionate;

n-amyl α2,6-diethylanilino-propionate;

n-hexyl α2,6-diethylanilino-propionate;

n-heptyl α2,6-diethylanilino-propionate;

allyl α2,6-diethylanilino-propionate;

crotonyl α2,6-diethylanilino-propionate;

propargyl 2,6-diethylanilino-acetate;

Halogeno-fatty acid halide:

monochloroacetic acid chloride;

monobromoacetic acid chloride;

monoiodoacetic acid chloride;

monofluoroacetic acid chloride;

monochloroacetic acid bromide;

monobromoacetic acid bromide;

monoiodoacetic acid bromide;

monofluoroacetic acid bromide;

dichloroacetic acid chloride;

dibromoacetic acid chloride;

trichloroacetic acid chloride;

trifluoroacetic acid chloride;

α,α-dichloropropionic acid chloride;

α ,α,β,β-tetrafluoropropionic acid chloride,

Halogeno-fatty acid anilide;

2,6-dimethyl-monochloroacetic acid anilide;

2,6-dimethyl-monobromoacetic acid anilide;

2,6-dimethyl-monoiodoacetic acid anilide;

2,6-dimethyl-monofluoroacetic acid anilide;

2,6-dimethyl-dichloroacetic acid anilede;

2,6-dimethyl-trichloroacetic acid anilide;

2,6-dimethyl-trifluoroacetic acid anilide;

2,6-dimethyl-α,α-dichloropropionic acid anilide;

2-methyl-6-ethyl-monochloroacetic acid anilide;

2-methyl-6-ethyl-monobromoacetic acid anilide;

2-methyl-6-ethyl-monoiodoacetic acid anilide;

2-methyl-6-ethyl-monofluoroacetic acid anilide;

2-methyl-6-ethyl-trichloroacetic acid anilide;

2-methyl-6-ethyl-α,α,β,β-tetrafluoropropionic acid anilide;

2,6-diethyl-monochloroacetic acid anilide;

2,6-diethyl-monobromoacetic acid anilide;

2,6-diethyl-monoiodoacetic acid anilide;

2,6-diethyl-monofluoroacetic acid anilide;

2,6-diethyl-trichloroacetic acid anilide;

2,6-diethyl-trifluoroacetic acid anilide;

2,6-diethyl-α,α-dichloropropionic acid anilide;

2,6-diethyl-α,α,β,β-tetrafluoropropionic acid anilide;

2,6-di-n-propyl-monochloroacetic acid anilide;

2,6-di-n-propyl-monobromoacetic acid anilide;

2,6-di-n-propyl-monoiodoacetic acid anilide;

2,6-di-n-propyl-monofluoroacetic acid anilide;

2,6-di-n-propyl-trichloroacetic acid anilide;

2,6-di-n-propyl-α,α-dichloropropionic acid anilide;

2,6-di-n-propyl-dichloroacetic acid anilide;

2,6-di-n-propyl-trifluoroacetic acid anilide;

Halogeno-fatty acid and the ester derivative thereof.

monochloroacetic acid;

methyl monochloroacetate;

ethyl monochloroacetate;

n-propyl monochloroacetate;

iso-propyl monochloroacetate;

n-butyl monochloroacetate;

iso-butyl monochloroacetate;

monobromoacetic acid;

methyl monobromoacetate;

ethyl monobromoacetate;

n-propyl monobromoacetate;

n-butyl monobromoacetate;

propargyl monobromoacetate;

monoiodoacetic acid;

methyl monoiodoacetate;

ethyl monoiodoacetate;

n-propyl monoiodoacetate;

n-butyl monoiodoacetate;

dichloroacetic acid;

methyl dichloroacetate;

ethyl dichloroacetate;

n-propyl dichloroacetate;

trichloroacetic acid;

methyl trichloroacetate;

ethyl trichloroacetate;

n-butyl trichloroacetate;

α,α-dichloropropionic acid;

methyl α,α-dichloropropionate;

ethyl α,α-dichloropropionate;

α,α-β,β-tetrafluoropropionic acid;

methyl α,α-β,β-tetrafluoropropionate;

ethyl α,α-β,β-tetrafluoropropionate;

n-propyl α,α,β,β-tetrafluoropropionate;

In a practical application, the compounds of the present invention maybe spread as such, or may be used in any form of granule, wettablepowder, emulsion, and dust.

As the solid carriers used in preparing these preparations, there areillustrated, for example, talc, bentonite, clay, kaolin, diatomaceousearth, vermiculite, slaked lime, etc. and, as the liquid carriers, thereare illustrated benzene, toluene, xylene, alcohols, acetone,methylnaphthalene, diozane, cyclohexanone, etc. As the emulsifyingagents, there are illustrated alkylsulfuric esters, alkylsulfonate,arylsulfonate, polyethylene glycol ethers, polyhydric alcohol esters,etc.

In a practical application, a speader such as a surface active agentused in agricultural field may of course be mixed so as to improve andensure the herbicidal effect, and, it is also possible to use incombination with other agricultural chemicals such as fungicides,insecticides, herbicides, etc., or with fertilizers.

The combination examples of the composition of the present invention areshown below.

EXAMPLE 1

25 Parts by weight of N-chloroacetyl-2,6-diethylanilinoacetic acid, 5parts by weight of polyoxyethylene acetylaryl ester surface active agentand 70 parts by weight of talc are well crushed and mixed to obtain awettable powder.

EXAMPLE 2

25 Parts by weight of N-chloroacetyl-2,6-dimethylanilinoacetic acidn-amyl ester, 5 parts by weight of polyoxyethylene acetylaryl estersurface active agent and 70 parts by weight of talc are well crushed andmixed to obtain a wettable powder.

EXAMPLE 3

30 Parts by weight of ethyl N-chloroacetyl-2,6-diethylanilinoacetate, 20parts by weight of polyethylene glycol ether surface active agent and 50parts by weight of cyclohexanone are well mixed to obtain an emulsion.

EXAMPLE 4

30 Parts by weight of n-decyl N-chloroacetyl-2,6-diethylanilino-acetate,20 parts by weight of polyethylene glycol ether surface active agent and50 parts by weight of cyclohexanone are well mixed to obtain anemulsion.

EXAMPLE 5

8 Parts by weight of ethyl N-chloroacetyl-2,6-diethylanilinoacetate, 38parts by weight of bentonite, 50 parts by weight of clay and 4 parts byweight of sodium lignin sulfonate are well crushed and mixed, and, afterwell kneading with the addition of water, granulated and dried to obtaina granule.

EXAMPLE 6

8 Parts by weight of allyl N-dichloroacetyl-2,6-diethylanilinoacetate,38 parts by weight of bentonite, 50 parts by weight of clay and 4 partsby weight of sodium lignin sulfonate are well crushed and mixed, and,after kneading with the addition of water, granulated and dried toobtain a granule.

The present invention will be explained in greater detail by thefollowing Examples, but not limited only to them as a matter of course.

EXAMPLE 7

23.5 Grams (0.1 mol) of ethyl 2,6-diethylanilinoacetate and 11.3 g (0.1mol) of monochloroacetic acid chloride were dissolved in 100 ml ofbenzene, 11.0 g of triethylamine was then added dropwise thereto withstirring maintaining the reaction temperature at 10°-20° C. and,thereafter, stirring was continued for further 2 hours at a roomtemperature. The reaction solution was washed with successive, 5% sodiumhydroxide aqueous solution, 5% hydrochloric acid aqueous solution, andwater. Then, the benzene layer was dried over anhydrous sodium sulfate.Thereafter, benzene was removed under reduced pressure to obtain the endproduct, ethyl N-chloroacetyl-2,6-diethylanilinoacetate. n_(D) ²⁶ :1.5225.

    ______________________________________                                        Elementary analysis:                                                                         C (%) H (%)   N (%)   Cl (%)                                   ______________________________________                                        Calculated for C.sub.16 H.sub.22 NClO.sub.3                                                    61.63   7.11    4.49  11.37                                  Found:           61.81   7.08    4.42  11.48                                  ______________________________________                                    

The results obtained in the similar manner as above shown in thefollowing Table 1.

                                      TABLE 1                                     __________________________________________________________________________    Anilino-                                                                      fatty   Halogeno-                                                                            Nhalogenoacylanilino-fatty acid or the ester                   acid or acetic derivative thereof                                             Ex.                                                                              the ester                                                                          acid                   Physical                                                                            Yield                                                                             Elementary analysis                  No.                                                                              thereof                                                                            halide Chemical structure                                                                            constant                                                                            (%) C (%)                                                                             H (%)                                                                             N (%)                                                                             Cl                       __________________________________________________________________________                                                         (%)                      8  Ethyl 2,6- dimethyl- anilino- acetate                                              ClCH.sub.2 COCl                                                                       ##STR5##       n.sub.D.sup.23 1.3647 bp.sub.0.4 136-138.de                                   gree. C.                                                                            85  Calcd.: 59.266.394.9412.50                                                    Found: 59.376.285.0212.51            9  Ethyl 2-methyl- 6-ethyl- anilino- acetate                                          ClCH.sub.2 COCl                                                                       ##STR6##       n.sub.D.sup.22 1.5271 bp.sub.0.7 161-163.de                                   gree. C.                                                                            88  Calcd.: 60.506.774.7016.12                                                    Found: 60.476.854.6616.23            10 Ethyl 2.6- dimethyl- anilino- acetate                                              Cl.sub.3 CCOCl                                                                        ##STR7##       n.sub.D.sup.21.5 1.4230 bp.sub.0.6                                            162-163° C.                                                                  75  Calcd.: 47.684.573.9730.16                                                    Found: 47.544.543.8730.20            __________________________________________________________________________

EXAMPLE 11

22.6 Grams (0.1 mol) of 2.6-diethyl-chloroacetonailide was dissolved in100 ml of tetrahydrofuran, and 45 g of n-hexane solution containing 15%of n-butyl lithium was gradually added dropwise thereto at a roomtemperature with stirring. Furthermore, 12.3 g (0.1 mol) of ethylmonochloroacetate was added thereto, and the mixture was refluxed for 4hours. After cooling, 20 g of ethanol was added to the reaction mixture,and the solvent was removed under reduced pressure. The resultingresidue was extracted with 100 ml of diethyl ether. After washing withwater, the ether layer was dried over anhydrous sodium sulfate, and thesolvent was removed to obtain 24.9 g of the end product, ethylN-chloroacetyl-2,6-diethylanilinoacetate. n_(D) ²⁴ : 1.5228.

    ______________________________________                                        Elementary analysis:                                                                       C (%) H (%)    N (%)   Cl (%)                                    ______________________________________                                        Calcd. for C.sub.16 H.sub.22 NClO.sub.3 :                                                    61.63   7.11     4.49  11.37                                   Found:         61.77   7.20     4.46  11.22                                   ______________________________________                                    

The results obtained in the similar manner as above are shown in thefollowing Table 2.

                                      TABLE 2                                     __________________________________________________________________________              Halogeno-                                                           Mono-     fatty Nhalogenoacylanilino-fatty acid or the ester                  halogeno- acid or                                                                             derivative thereof obtained                                   Ex.                                                                              acetic the ester             Physical                                                                            Yield                                                                             Elementary analysis                 No.                                                                              acid amide                                                                           thereof                                                                             Chemical structure                                                                            constant                                                                            (%) C (%)                                                                             H (%)                                                                             N (%)                                                                             Cl                      __________________________________________________________________________                                                          (%)                     11 N(2,6-di- methyl- phenyl) monochloro- acetamide                                      Ethyl mono- chloro- acetate                                                          ##STR8##       n.sub.D.sup.23 1.3645 bp.sub.0.35                                             134-137° C.                                                                  78  Calcd.: 59.266.394.9412.50                                                    Found: 59.416.494.8112.57           12 N(2- methyl- 6-ethyl- phenyl)- monochloro- acetamide                                 Ethyl mono- bromo- acetate                                                           ##STR9##       n.sub.D.sup.22 1.5274 bp.sub.0.7 160-164.d                                    egree. C.                                                                           69  Calcd.: 60.506.774.7016.12                                                    Found: 60.546.694.8316.14           13 N(2,6-di- ethyl- phenyl) monochloro- acetamide                                       Butyl mono- chloro- acetate                                                          ##STR10##      n.sub.D.sup.23.5 1.5176                                                             86  Calcd.: 63.217.714.1210.43                                                    Found: 63.597.824.2910.37           __________________________________________________________________________

EXAMPLE 14

24.7 Grams of allyl 2,6-diethylanilinoacetate and 11.3 g ofmonochloroacetic acid chloride were dissolved in 100 ml of benzene, 11.0g of triethylamine was then added dropwise thereto with stirringmaintaining the reaction temperature at 10°-20° C., and, thereafter,stirring was continued for further 2 hours at a room temperature. Thereaction solution was washed with successive, 5% sodium hydroxideaqueous solution, 5% hydrochloric acid aqueous solution, and water.Then, the benzene layer was dried over anhydrous sodium sulfate.Thereafter, benzene was removed under reduced pressure to obtain the endproduct, allyl N-chloroacetyl-2,6-diethylanilinoacetate. n_(D) ²¹.5 :1.5288.

    ______________________________________                                        Elementary analysis:                                                                       C (%) H (%)    N (%)   Cl (%)                                    ______________________________________                                        Calcd. for C.sub.17 H.sub.22 NClO.sub.3 :                                                    63.05   6.85     4.33  10.95                                   Found:         63.09   6.85     4.19  10.88                                   ______________________________________                                    

The results obtained in the similar manner as above are shown in thefollowing Table 3.

    TABLE 3      Nhalogenoacylanilino-fatty acid ester obtained Example Anilino-fatty     acid ester Halogeno-fatty Physical Yield Elementary analysis No. used     acid halide used Chemical structure constant (%) C (%) H (%) N (%) Cl     (%)         15      ##STR11##      ClCH.sub.2      COCl     ##STR12##      n.sub.D.sup.24 1.5263 86 Calcd.:62.677.424.3010.88Found:62.547.584.2010.     81      16     ##STR13##      ClCH.sub.2      COBr     ##STR14##      n.sub.D.sup.23 1.5297 71 Calcd.:67.989.033.308.36Found:68.058.993.348.16      17     ##STR15##      Cl.sub.2      CHCOCl     ##STR16##      n.sub.D.sup.23 1.5376 82 Calcd.:56.995.913.9119.79Found:57.185.773.9019.     75      18     ##STR17##      BrCH.sub.2      COCl     ##STR18##      n.sub.D.sup.22 1.5325 77 Calcd.:56.556.333.6620.90Found:56.726.303.8721.     11      19     ##STR19##      Cl.sub.3      COOCl     ##STR20##      n.sub.D.sup.23 1.5441 65 (Bromine)55.256.033.2224.46Found:55.346.163.242     4.53      20     ##STR21##      ClCH.sub.2      COCl     ##STR22##      n.sub.D.sup.22.5 1.5408 84 Calcd.:63.456.264.3511.02Found:63.526.484.171     0.94

TEST EXAMPLE 1

Barnyard grass and large crabgrass as the representative of grassyweeds, and radish and red root pigweed as the representative ofbroad-leaf plants each was sown in an unglazed flower pot of 12 cm indiameter, and, after covering with the soil, treated with the chemicals.Thereafter, these plants were reared in a greenhouse, and the herbicidaleffect was observed 20 days after the treatment. The results are shownin Table 4. The estimation of the herbicidal effect is expressed bynumerals of from 0 (no injuries) to 5 (completely dead). All thecompounds were used in the form of wettable powder diluted with water.

                  TABLE 4                                                         ______________________________________                                                           Herbicidal effect                                                      Applied  Barn-   large                                                        amount   yard    crab- red root                                                                             Ra-                                 Compound    (g/10a)  grass   grass pigweed                                                                              dish                                ______________________________________                                        N--chloroacetyl-                                                                          125      5       5     5      0                                   2,6-diethyl-                                                                              63       5       5     4      0                                   anilinoacetic                                                                             32       5       5     2      0                                   acid ethyl ester                                                                          16       5       4     1      0                                   Ethyl N--chloro-                                                                          125      5       5     5      0                                   acetyl-2-methyl-                                                                          63       5       5     3      0                                   6-n-propyl- 32       5       5     1      0                                   anilinoacetate                                                                2-chloro-2',6'-                                                                           125      5       4     2      0                                   diethylaceto-                                                                             63       4       4     0      0                                   anilide*    32       1       1     0      0                                   n-Amyl N--chloro-                                                                         125      5       5     5      0                                   acetyl-2,6- 63       5       5     3      0                                   dimethylanilino-                                                                          32       4       5     1      0                                   acetate                                                                       Allyl N--dichloro-                                                                        125      5       5     5      0                                   acetyl-2,6-diethyl-                                                                       63       5       5     4      0                                   anilinoacetate                                                                            32       5       5     2      0                                   2-Chloro-2' ,6'-                                                                          125      5       4     2      0                                   diethylaceto-                                                                             63       4       4     0      0                                   anilide*    32       1       1     0      0                                   ______________________________________                                         *Control Compound                                                        

TEST EXAMPLE 2

1.5 Kg of paddy field soil was placed in each of Wagner pot of 14 cm indiameter, and the pots were brought into a paddy field state.Thereafter, third-leaf period rice seedlings were transplanted to thepot, which was further sown with the seeds of barnyard grass, and thewater-flooded soil was treated with prescribed amount of the chemicals.On the 25th day after the treatment with the chemicals, the herbicidaleffect and the degree of phytotoxicity were investigated about thetransplanted or sown plants described above, and the spontaneouslygenerated broad-leaf weeds such as monochoria, false pimpernel, Rotalaindica Koehne, etc. and slender spikerush. The chemicals were applied inthe form of an emulsion prepared according to the same prescription asin the Example 2 described above. The results are shown in Table 5. Theestimations of herbicidal effect and phytotoxicity were expressed bynumerals of 0-5 as follows.

    ______________________________________                                        0        Action on plants                                                                              Nothing                                              1        Action on plants                                                                              Slight                                               2        Action on plants                                                                              Small                                                3        Action on plants                                                                              Middle                                               4        Action on plants                                                                              Large                                                5        Action on plants                                                                              Completely dead                                      ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                        Water-flooded soil treatment test.                                                         Phyto-                                                           Applied      toxi-   Herbicidal effect                                                amount   city    Barnyard                                                                             Broad-leaf                                                                            Slender                               Compound                                                                              (g/10a)  to rice grass  weeds   spikerush                             ______________________________________                                        Ethyl N--                                                                             63       0       5      5       3                                     chloro- 32       0       5      5       2                                     acetyl-2,                                                                             16       0       5      4       0                                     6-diethyl-                                                                             8       0       5      2       0                                     anilino-                                                                      acetate                                                                       Ethyl N--                                                                             63       0       5      5       3                                     chloro- 32       0       5      5       2                                     acetyl-2-                                                                             16       0       5      3       0                                     methyl-6-                                                                     n-propyl-                                                                     anilino-                                                                      acetate                                                                       Butyl N--                                                                             63       0       5      5       4                                     chloro- 32       0       5      5       3                                     acetyl-2,                                                                             16       0       5      4       0                                     6-diethyl-                                                                    anilino-                                                                      acetate                                                                       2-Chloro-                                                                             63       0       5      3       0                                     2,6-diethyl-                                                                          32       0       4      0       0                                     acetanilide*                                                                          16       0       2      0       0                                     n-Amyl N--                                                                            63       0       5      5       3                                     chloro- 32       0       5      5       2                                     acetyl-2,                                                                             16       0       5      3       0                                     6-dimethyl-                                                                   anilino-                                                                      acetate                                                                       Allyl N--                                                                             63       0       5      5       3                                     dichloro-                                                                             32       0       5      5       3                                     acetyl-2,6-                                                                           16       0       5      4       1                                     diethyl-                                                                      anilino-                                                                      acetate                                                                       2-Chloro-                                                                             63       0       5      3       0                                     2',6'-di-                                                                             32       0       4      0       0                                     ethylacet-                                                                            16       0       2      0       0                                     anilide*                                                                      ______________________________________                                         *Control compound                                                        

What is claimed is:
 1. A herbicidal composition comprising aherbicidally effective amount of N-halogenoacylanolino-fatty acid or theester derivative thereof represented by the general formula: ##STR23##wherein R₁ and R₂ each represents C₁ -C₄ alkyl, R₃ represents a hydrogenatom, alkyl having up to 10 carbon atoms, C₃ -C₄ alkenyl, propargyl orcyclohexyl, R₄ represents C₁ -C₃ alkyl substituted by 1-4 halogen atomsand Y represents C₁ -C₃ alkylene, as an effective ingredient, and aherbicidally acceptable inert carrier.
 2. The herbicidal compositionaccording to claim 1, wherein said effective ingredient is the compoundof the formula: ##STR24## wherein R₁, R₂, R₃ and R₄ are the same asdefined in claim
 1. 3. The herbicidal composition according to claim 1,wherein said effective ingredient is the compound of the formula:##STR25##
 4. The herbicidal composition according to claim 1, whereinsaid effective ingredient is the compound of the formula: ##STR26## 5.The herbicidal composition according to claim 1, wherein said effectiveingredient is the compound of the formula: ##STR27##
 6. A method ofcontrolling weeds which comprises applying an effective amount of acomposition containing N-halogenoacylanilino-fatty acid or the esterderivative thereof of the formula: ##STR28## wherein R₁ and R₂ eachrepresents C₁ -C₄ alkyl, R₃ represents a hydrogen atom, alkyl having upto 10 carbon atoms, C₃ -C₄ alkenyl, propargyl or cyclohexyl, R₄represents C₁ -C₃ alkyl substituded by 1 to 4 halogen atoms and Yrepresents C₁ -C₃ alkylene, as an effective ingredient, to the weeds. 7.A method for controlling the growth of undesirable weeds which comprisesapplying a herbicidally effective amount of a compound of the formula:##STR29## wherein R₁, R₂ and R₃ individually are methyl or ethyl and xis chlorine.
 8. The method according to claim 1, wherein said effectiveingredient is the compound of the formula: ##STR30## wherein R₁, R₂, R₃and R₄ are the same as defined in claim
 6. 9. The method according toclaim 6, wherein said effective ingredient is the compound of theformula: ##STR31##
 10. The method according to claim 6, wherein saideffective ingredient is the compound of the formula: ##STR32##
 11. Themethod according to claim 6, wherein said effective ingredient is thecompound of the formula: ##STR33##